Compounds containing an isocyanate group have widely been used in the field of polymer chemistry because of their excellent reactivities. Particularly, compounds containing both a polymeric carbon-carbon unsaturated group and an isocyanate group in the same molecule can be used for a wide variety of industrial fields because each functional group respectively contributes to various reactions in different reaction mechanism. By paying attention to such an usefulness, the present inventors have already provided an acylisocyanate compound represented by the formula: ##STR1## [wherein R is a lower alkyl group] (U.S. Pat. No. 4,925,982).
The above acylisocyanate compound [I] is generally liquid which is stable at a normal temperature and is easily handled. Further, it contains a polymeric carbon-carbon unsaturated group and an isocyanate group in a molecule and a carbonyl group is also present between both functional groups while adjoining them and, therefore, activity of the carbon-carbon unsaturated group as well as that of the isocyanate group are enhanced. Thus, it is in such a state that various addition reactions can be conducted. Namely, various reactions (e.g. radical polymerization, anion polymerization, dimerization, trimerization, polarity addition, active hydrogen addition, etc.) based on the part A (conjugated double bond) and part B (acylisocyanate group) of the following formula: ##STR2## [wherein R is as defined above] can be conducted by the acylisocyanate compound [I].
Accordingly, it is expected that the acylisocyanate compound [I] is widely used in chemical industry as reactive materials.
For example, the present inventors have already disclosed that a compound represented by the formula: ##STR3## [wherein each R is the same or different and is as defined above] (Japanese Patent Kokai No. 60-231644 corresponding to U.S. Pat. No. 4,935,413) and a compound represented by the formula: ##STR4## [wherein R is as defined above, and Z is an organic group containing a tertiary amino group] (Japanese Patent Kokai No. 61-17554 corresponding U.S. Pat. No. 4,935,413) are useful in the fields of coatings, plastics and the like.
Under these circumstances, the present inventors have found that the diene structure part B (acylisocyanate group) containing a hetero atom in the acylisocyanate compound (I) makes a cyclic addition reaction with a suitable dienophile to form a novel heterocyclic compound, and the above heterocyclic compound can further make a cyclic addition reaction with the suitable dienophile to form an additional novel heterocyclic compound, and the present invention has been completed.